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Family-friendly vacation rentals in Grassina

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Popular amenities for Grassina family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost

Home in Gaiole In Chianti

4.86 out of 5 average rating, 248 reviews

Charming estate with views

MoritzRating, 5 stars1 month ago
We loved Bernardino's place. It was super cozy, the garden and whirlpool were amazing. The kitchen had everything we needed. And Bernardino was super helpful with tips and answers to all our questions. Highly recommend if you're looking for a remote place to enjoy Tuscany.
Guest favorite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 172 reviews

Ancient Casolare Toscano on the Chianti hills

SandraRating, 5 stars3 weeks ago
Giovanni's property exceeded our expectations in every way! From the warm welcome with a delicious charcuterie board and homemade wine to the exceptional hospitality throughout our stay. Giovanni was an outstanding host, providing invaluable suggestions and insider tips for exploring the area. Highly recommend Giovanni's property for its stunning beauty, warm hospitality, and unique experiences. We wished we had booked more nights to fully enjoy the property's amenities, including the olive pressing experience, which unfortunately we ran out of time.
Guest favorite

Apartment in Centro Storico

4.93 out of 5 average rating, 279 reviews

M&G Apartment your home away from home

RyanRating, 5 stars1 week ago
Massimiliano was gracious and friendly. The location is great for those willing and able to walk 15-30 minutes as that will get you to countless trattorias, cafes, and museums. If you are visiting from a city, this apt will feel like home. If you are from a quiet suburb or town, be aware that weekend nights will be filled with people in the streets until the wee hours. We would gladly stay here again.
Guest favorite

Villa in San Casciano in Val di Pesa

4.94 out of 5 average rating, 160 reviews

The Vichiaccio Villa with Jacuzzi in Chianti

RyanRating, 5 stars3 weeks ago
A lovely home that has clearly been well cared for alongside a beautiful landscape of vineyards and olive groves. Our host was very attentive and available for any questions and we couldn't have had a nicer time.
Guest favorite

Apartment in Gavinana

4.96 out of 5 average rating, 391 reviews

Suite Michelangelo with Terrace

MariRating, 5 stars2 months ago
Spacious apartment, great kitchen, big bathroom and lovely balcony overlooking Florence. Luciano is a very nice and helpful host. The parking space we parked the car on as it was not needed during the stay. Instead we got the bus that stopped close to the apartment. We appreciated that there was coffee, cookies and other edible in the kitchen and that we didn't have to buy dish soap, toilet paper, paper towels, soap and shampoo. Thank you Luciano for your hospitality! We would be glad to come back!
Guest favorite

Condo in Centro Storico

4.9 out of 5 average rating, 100 reviews

Fortress area, Mansarda with terrace, Jacuzzi, A/C

FinlayRating, 5 stars1 month ago
We had a great time staying here! Very clean, cosy and comfortable, with lots of space and a lovely jet bath which was perfect for relaxing after the Firenze Marathon!
Guest favorite

Farm stay in Figline Incisa Valdarno

4.94 out of 5 average rating, 344 reviews

Romantic in bioagriturismo Florence

OfeliaRating, 5 stars1 week ago
The room was very spacious, comfortable and quiet. Francesca was very welcoming. The breakfast basket was a delicacy that you cannot miss. We also found a lot of wild animals nearby. People who like animals and quietness must not miss it. And we only found out that we forgot to leave the room key after we left. Later we drove back to return the key. I apologize to Francesca again for causing you unnecessary trouble.
Guest favorite

Loft in Centro Storico

4.96 out of 5 average rating, 422 reviews

Little Jewel Florence , Dome, David, - Garage

YumikoRating, 5 stars1 month ago
This room receives the morning sun. Surrounded by antique furniture, you will feel like you are living here. Once you step out of the building, you can enjoy the wonderful view of the Duomo. Riccardo has taken care of me in many ways.Thank you,Riccardo!

Family- and pet-friendly home rentals

Guest favorite

Home in Radda In Chianti

4.84 out of 5 average rating, 173 reviews

Tuscany House "La Querce Sola"

LeifRating, 5 stars3 months ago
Beautiful home with a gorgeous view of the Tuscan hills! Peaceful but still accessible to everything in area within an hour drive. We were definitely glad to have an SUV as our rental car, as the dirt road into the property is very bumpy. Rosanna was super friendly and accommodating - would definitely recommend staying here!
Guest favorite

Guest suite in Centro Storico

4.95 out of 5 average rating, 164 reviews

A stone's throw from downtown and away from the chaos

AnnyRating, 5 stars1 month ago
I had a great time exploring Florence — and Italy as a whole — for the first time, and felt right at home thanks to Ms Stefania. Meeting her family and staying under their wing is a memory of its own. We maintained contact throughout my stay, with Ms Stefania checking in on me and ensuring my satisfaction. I even had the pleasure of meeting her pets up close and personal! The neighborhood was an eye candy with its picturesque buildings and narrow streets. As a solo female traveler, I felt as safe walking alone at night as I do at my own home. I couldn’t recommend Ms Stefania’s home enough and look forward to booking again in the future!
Superhost

Home in Borgo San Lorenzo

4.82 out of 5 average rating, 303 reviews

Mugello Countryside House

StephenRating, 5 stars2 months ago
Me and my wife had a wonderful stay at Lucrezia’s place, which offers a perfect blend of country charm just outside Florence. It’s conveniently located for a quick drive or train into the city whenever needed. The accommodations are both relaxing and comfortable, with everything you need to prepare meals at home. Lucrezia also recommended a fantastic local restaurant that exceeded my expectations. The property’s location is ideal, and I definatly recommend it to anyone looking for a peaceful getaway!
Guest favorite

Home in Rifredi

4.87 out of 5 average rating, 128 reviews

From Chiara - Your City Countryside

IanRating, 5 stars1 month ago
Aldo was a lovely host! He came to the airport to pick us up and take us to the flat. The flat is in an olive grove and the harvest was under way when we were there. Aldo gave us a bottle of the their freshly pressed olive oil. Delicious!
Superhost

Home in Centro Storico

4.85 out of 5 average rating, 439 reviews

San Gallo Suite in Florence Center

CarlosRating, 5 stars4 weeks ago
My gf and I loved Agnese’s apartment. Everything was within walking distance and yet felt far away enough from all the crowds and noise. This was the largest airbnb we stayed at throughout our trip by far so that was nice to have all the space! And we also had a cab scheduled by Agnese on our check out date. She was very responsive and kind and I would stay here again next time I come visit.
Guest favorite

Vacation home in Panzano In Chianti

4.97 out of 5 average rating, 141 reviews

Fienile Santa Teresa

MarnieRating, 5 stars2 months ago
Very private and peaceful. Beautiful view and the house was well equipped and comfortable. Host was very responsive and helpful.
Superhost

Condo in Castelfranco di Sopra

4.83 out of 5 average rating, 232 reviews

House between Firenze, Arezzo, chianti e Siena

VasundharaRating, 5 stars2 months ago
Splendid location and excellent food! Perfect getaway in my opinion — I saw the prettiest sunset of my life surrounded by cats and ducks.
Superhost

Apartment in Scandicci

4.86 out of 5 average rating, 140 reviews

Casa Gina - Welcome in Italy! Happy June 20% off

BárbaraRating, 5 stars6 months ago
We had a great stay in Davide’s place. Easy to reach Florence by tram and very nice neighborhood.

Family-friendly home rentals with a pool

Guest favorite

Villa in Panzano In Chianti

4.93 out of 5 average rating, 70 reviews

Luxury Villa on Chianti Wine Estate

ErinRating, 5 stars1 month ago
Our stay at the villa felt like living in a postcard- breathtaking surroundings! The historic villa was charming and comfortable for our group of 5. The area is idyllic and the onsite winery is a fantastic plus. We enjoyed the fireplace and the outdoor areas. Great laundry facilities as well . Vicky was very helpful and gave us great advice on local sites. We would definitely return !
Guest favorite

Apartment in Gaiole In Chianti

4.76 out of 5 average rating, 21 reviews

Idyllic with shared pool in the heart of Chianti

GuidoRating, 5 stars4 months ago
Heidi's apartment is situated in a larger complex on the outskirts of the village, just a short walk from the town center where you can find a church, a mini supermarket, bars, and a popular restaurant that is always fully booked. The village is ideally located in the heart of Chianti, making it a perfect starting point for exploring the region. You can drive along one of the scenic, winding roads to a wine tasting event, enjoy a bike ride through the picturesque countryside, or visit nearby cities like Siena or Florence (Firenze). One of the highlights of the apartment is the spacious swimming pool (1.35 m deep), which is perfect for cooling off during the hot summer days, especially if you have kids. The apartment itself is well-equipped, ensuring a comfortable stay. Communication with Heidi is easy and friendly. She provides detailed information on the check-in and check-out procedures, as well as instructions for using various amenities in the complex. We enjoyed our stay!
Superhost

Farm stay in Reggello

4.87 out of 5 average rating, 127 reviews

Holiday accommodation in Tuscany

DaraRating, 5 stars2 months ago
Ewa was such a friendly host. She worked with us, despite us having some changes in our arrival plan. The place was clean and the kitchen was very well-stocked with pots, plates, pans, utensils, which was useful for us as a vegetarian family with allergies. My family had never had an agriturismo experience, and Ewa made it an amazing one. Tip: try her amazing olive oil and pick some up before you leave!
Guest favorite

Hut in Poggibonsi

4.94 out of 5 average rating, 129 reviews

Lovely barn with pool between Siena and Florence

JamieRating, 5 stars2 months ago
Great stay here during our time in Tuscany. The roads can be as you approach Michele's place so definitely recommend a small suv or something like that. Michele's was very friendly and flexible on things and even brought us a few things to do laundry with. There are two sweet cats that live on the property and one will come and greet you every morning if you're nice to it. We stayed here while spending time in Florence, Siena and the town of Poggibonsi is about 15 minutes away if you need groceries or a close dinner.
Guest favorite

Apartment in La Felce

4.98 out of 5 average rating, 107 reviews

La Felce Country House

GarrettRating, 5 stars3 months ago
Cristina is the ultimate host! Everything was immaculate and set up for us. We traveled with two young kids, and she was proactively prepared with a crib & high chair. She also had amazing recommendations and answered any questions for us. Led us to a spectacular sunset winery in the hills. The premise has stunning views and hanging poolside in the mountains, was just what the doctor ordered. Highly recommended and makes you feel like family!
Guest favorite

Farm stay in Passo dei Pecorai

4.94 out of 5 average rating, 70 reviews

Charming Cottage among vineyards with private pool

JessicaRating, 5 stars2 months ago
I loved our stay at this beautiful Tuscan villa! We had such a wonderful experience and Olivia was SO helpful! The grounds are gorgeous, the wine was amazing. My only regret was not staying longer than three days! I hope to return to Casavecchia de Nozzole again!
Guest favorite

Villa in Certaldo (FI)

4.89 out of 5 average rating, 143 reviews

Tuscan farmhouse with private pool and views

DorothyRating, 5 stars2 months ago
Fantastic accommodation with lovely views of the countryside. Especially loved the fire place and large spacious kitchen. Charley and Ann were very gracious hosts and I would have no problem recommending this accommodation to anyone who wants to visit Tuscany. The accommodation was within 30 mins of most tourist towns and trains which made it excellent for day trips.
Superhost

Home in Firenze

4.89 out of 5 average rating, 152 reviews

Il Melograno, Florence hills & pool & olive oil

JamesRating, 5 stars1 month ago
We had a great stay. Great spot for families, close enough to Florence to walk but far enough away to relax. We even had the opportunity to help pick olives. The kids loved the tree house and trampoline.

Quick stats about vacation rentals that are family-friendly in Grassina

  • Total rentals

    30 properties

  • Nightly prices starting at

    $100 before taxes and fees

  • Total number of reviews

    590 reviews

  • Rentals with a pool

    30 properties have a pool

  • Wifi availability

    30 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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